US5869441A - Bar compositions comprising novel chelating surfactants - Google Patents

Bar compositions comprising novel chelating surfactants Download PDF

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US5869441A
US5869441A US08/869,397 US86939797A US5869441A US 5869441 A US5869441 A US 5869441A US 86939797 A US86939797 A US 86939797A US 5869441 A US5869441 A US 5869441A
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total composition
surfactants
edta
surfactant
composition
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Michael Fair
Mengtao He
Michael Massaro
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Lever Brothers Co
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Lever Brothers Co
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Assigned to LEVER BROTHERS COMPANY, DIVISION OF CONOPCO, INC. reassignment LEVER BROTHERS COMPANY, DIVISION OF CONOPCO, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: FAIR, MICHAEL, HE, MENGTAO, MASSARO, MICHAEL
Priority to US08/869,397 priority Critical patent/US5869441A/en
Priority to DE69807686T priority patent/DE69807686T2/de
Priority to CA002291029A priority patent/CA2291029A1/en
Priority to AU82114/98A priority patent/AU8211498A/en
Priority to ES98932097T priority patent/ES2183388T3/es
Priority to PCT/EP1998/003184 priority patent/WO1998055571A1/en
Priority to EP98932097A priority patent/EP0986628B1/en
Priority to IN345BO1998 priority patent/IN189873B/en
Priority to ZA9804898A priority patent/ZA984898B/xx
Priority to ARP980102668A priority patent/AR015386A1/es
Publication of US5869441A publication Critical patent/US5869441A/en
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/94—Mixtures with anionic, cationic or non-ionic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0047—Detergents in the form of bars or tablets
    • C11D17/006—Detergents in the form of bars or tablets containing mainly surfactants, but no builders, e.g. syndet bar
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/04—Carboxylic acids or salts thereof

Definitions

  • the present invention relates to personal wash beauty bar compositions, particularly compositions comprising (1) novel EDTA-derived chelating anionic surfactants, preferably in combination with other types of anionic surfactants; and (2) one or more amphoteric surfactants.
  • the invention relates to the incorporation of the novel EDTA-derived chelating surfactants into specific bar skin cleansing formulation bases. Through careful balancing of the anionic, amphoteric and optional nonionic surfactants, and through specific handling of the novel chelating surfactants during processing, ultra formulation mildness to skin is achieved without sacrificing other desired user properties, such as rich and creamy lather.
  • EDTA Hydrophobically modified ethylenediaminetriacetic acid
  • EDTA-derived surfactants are ultra-mild to skin
  • inclusion of the surfactants into a personal washing bar is fraught with difficulties.
  • the lather produced by the chelating surfactant alone is not as satisfactory as that of a conventional anionic detergent (e.g., sodium lauryl ether sulfate).
  • aqueous solutions of the EDTA surfactants at the concentrations relevant to the personal washing have a viscosity which is too low to deliver the desired sensory cues.
  • the present invention comprises personal wash bar compositions comprising:
  • composition of a structurant selected from the group consisting of alkylene oxide components having a molecular weight of from about 2,000 to about 25,000; C 8 to C 22 free fatty acids; C 2 to C 20 alkanols; paraffin waxes; and water soluble starches;
  • composition comprises inorganic salts with multivalent counterions (e.g., aluminum chloride).
  • multivalent counterions e.g., aluminum chloride
  • the application relates to a process for making a composition
  • a process for making a composition comprising:
  • composition of a structurant selected from the group consisting of alkylene oxide components having a molecular weight of from about 2,000 to about 25,000; C 8 to C 22 free fatty acids; C 2 to C 20 alkanols; paraffin waxes; and water soluble starches;
  • composition comprises inorganic salts with multivalent counterions (e.g., aluminum chloride);
  • multivalent counterions e.g., aluminum chloride
  • the present invention relates to novel personal washing bar compositions, particularly compositions in which the surfactant system comprises 1 to 40% wt. total composition of the salt or salts of hydrophobically modified ethylenediaminetriacetic acid, and additionally comprises one or more anionic surfactants and one or more amphoteric surfactants, wherein no more than 1% of said compositions comprise salts with multivalent counterions (high levels are associated with lather depression).
  • the surfactant system comprises 1 to 40% wt. total composition of the salt or salts of hydrophobically modified ethylenediaminetriacetic acid, and additionally comprises one or more anionic surfactants and one or more amphoteric surfactants, wherein no more than 1% of said compositions comprise salts with multivalent counterions (high levels are associated with lather depression).
  • the surfactant system comprises 1 to 40% wt. total composition of the salt or salts of hydrophobically modified ethylenediaminetriacetic acid, and additionally comprises one or more anionic surfactants and one or more
  • the invention relates to a process for forming such bar compositions while retaining mildness and lathering, and acceptable bar properties by ensuring that EDTA acid is first dispersed into structurant and subsequently adding sufficient caustic to neutralize the EDTA acid.
  • the personal wash bar compositions comprise:
  • hydrophobically modified ethylenediaminetriacetic acids have general structure as follows: ##STR3##
  • n is from 1 to 40.
  • the hydrophobically modified group may be C n H 2n-1 where n is 2 to 40 and if further unsaturation occurs, the group may be C n H 2n-3 where n is 3 to 40 and so forth.
  • the salts are the salts of one or more of the carboxylic acid groups.
  • anionic surfactants i.e., lathering surfactants
  • amphoteric and/or zwitterionic surfactants 1 to 20% by wt. total composition one or more amphoteric and/or zwitterionic surfactants; inclusion of the amphoteric and zwitterionic surfactants is a criticality and required because the amphoteric surfactants reduce the skin irritation potential of the anionic surfactants in (2) and enhance the lather performance; and
  • formulations of the invention preferably comprise no more than 1% wt. total composition of inorganic and organic salts of Calcium (Ca 2+ ), Magnesium (Mg 2+ ), Aluminum (Al 3+ ) and other multivalent metal counterions, and mixtures thereof; preferably said salts are excluded from the total composition; the restriction on the concentration of said salts is important because such salts tend to diminish the lather performance of the EDTA-derived surfactants.
  • multi-valence salts include, but are not limited to, Calcium Chloride, Magnesium Chloride, Aluminum Chloride, Magnesium sulfate, Magnesium Stearate, Calcium Laurate, etc.
  • the salt and/or salts of the hydrophobically modified ethylenediaminetriacetic acid are salts(s) of the N-acyl EDTA surfactants described in U.S. Pat. Nos. 5,177,243, 5,191,081, 5,191,106, 5,250,728, and 5,284,972, all of which are incorporated by reference into the subject application.
  • the synthesis, physical and physiological properties of the EDTA-derived surfactants are also summarized in an article published recently (Inform, Vol. 6 no.10, October 1995).
  • hydrophobically modified ethylenediaminetriactive acids have general structure as follows: ##STR4##
  • n is from 1 to 40.
  • the hydrophobically modified group may be C n H 2n-1 where n is 2 to 40 and if further unsaturation occurs, the group may be C n H 2n-3 where n is 3 to 40 and so forth.
  • the salts are the salts of one or more of the carboxylic acid groups.
  • the counterions which may be used for the EDTA derived surfactants of the subject invention include but are not limit to Sodium (Na + ), Potassium (K + ), ammonium (NH 4 + ), monoethanolamine, diethanolamine, triethanolamine, N-Propylamine, isopropylamine, and tris(hydroxymethyl aminomethane). As noted, multivalent counterions should be avoided.
  • the EDTA-derived surfactants comprise 1% to 40% of the total composition.
  • the surfactant should comprise at least 5%, preferably 8%, more preferably ⁇ 10% of the total anionic surfactants in the composition.
  • the anionic surfactant other than EDTA-derived surfactant may be, for example, an aliphatic sulfonate, such as a primary alkane (e.g., C 8 -C 22 ) sulfonate, primary alkane (e.g., C 8 -C 22 ) disulfonate, C 8 -C 22 alkene sulfonate, C 8 -C 22 hydroxyalkane sulfonate or alkyl glyceryl ether sulfonate (AGS); or an aromatic sulfonate such as alkyl benzene sulfonate.
  • a primary alkane e.g., C 8 -C 22
  • primary alkane e.g., C 8 -C 22
  • disulfonate C 8 -C 22 alkene sulfonate
  • C 8 -C 22 hydroxyalkane sulfonate C 8 -C 22 hydroxyal
  • the anionic may also be an alkyl sulfate (e.g., C 12 -C 18 alkyl sulfate) or alkyl ether sulfate (including alkyl glyceryl ether sulfates).
  • alkyl ether sulfates are those having the formula:
  • R is an alkyl or alkenyl having 8 to 18 carbons, preferably 12 to 18 carbons, n has an average value of greater than 1.0, preferably between 2 and 3; and M is a solubilizing cation such as sodium, potassium, ammonium or substituted ammonium. Ammonium and sodium lauryl ether sulfates are preferred.
  • the anionic may also be alkyl sulfosuccinates (including mono- and dialkyl, e.g., C 6 -C 22 sulfosuccinates); alkyl and acyl taurates, alkyl and acyl sarcosinates, sulfoacetates, C 8 -C 22 alkyl phosphates and phosphates, alkyl phosphate esters and alkoxyl alkyl phosphate esters, acyl lactates, C 8 -C 22 monoalkyl succinates and maleates, sulphoacetates, and acyl isethionates.
  • alkyl sulfosuccinates including mono- and dialkyl, e.g., C 6 -C 22 sulfosuccinates
  • alkyl and acyl taurates alkyl and acyl sarcosinates
  • sulfoacetates C 8 -C 22 al
  • Sulfosuccinates may be monoalkyl sulfosuccinates having the formula:
  • amido-MEA sulfosuccinates of the formula
  • R 4 ranges from C 8 -C 22 alkyl and M is a solubilizing cation
  • alkoxylated citrate sulfosuccinates and alkoxylated sulfosuccinates such as the following: ##STR5##
  • n 1 to 20; and M is as defined above.
  • R ranges from C 8 -C 20 alkyl and M is a solubilizing cation.
  • Taurates are generally identified by formula
  • R 2 ranges from C 8 -C 20 alkyl
  • R 3 ranges from C 1 -C 4 alkyl
  • M is a solubilizing cation.
  • carboxylates such as follows:
  • R is C 8 to C 20 alkyl; n is 0 to 20; and M is as defined above.
  • amido alkyl polypeptide carboxylates such as, for example, Monteine LCQ® by Seppic.
  • C 8 -C 18 acyl isethionates Another surfactant which may be used are the C 8 -C 18 acyl isethionates. These esters are prepared by reaction between alkali metal isethionate with mixed aliphatic fatty acids having from 6 to 18 carbon atoms and an iodine value of less than 20. At least 75% of the mixed fatty acids have from 12 to 18 carbon atoms and up to 25% have from 6 to 10 carbon atoms.
  • Acyl isethionates when present, will generally range from about 0.5-15% by weight of the total composition. Preferably, this component is present from about 1 to about 10%.
  • the acyl isethionate may be an alkoxylated isethionate such as is described in liardi et al., U.S. Pat. No. 5,393,466, hereby incorporated by reference into the subject application.
  • This compound has the general formula: ##STR6##
  • R is an alkyl group having 8 to 18 carbons
  • m is an integer from 1 to 4
  • X and Y are hydrogen or an alkyl group having 1 to 4 carbons
  • M + is a monovalent cation such as, for example, sodium, potassium or ammonium.
  • the anionic component will comprise from about 1 to 40% by weight of the composition, preferably 5 to 30%, most preferably 8 to 25% by weight of the composition.
  • Zwitterionic surfactants are exemplified by those which can be broadly described as derivatives of aliphatic quaternary ammonium, phosphonium, and sulfonium compounds, in which the aliphatic radicals can be straight or branched chain, and wherein one of the aliphatic substituents contains from about 8 to about 18 carbon atoms and one contains an anionic group, e.g., carboxy, sulfonate, sulfate, phosphate, or phosphonate.
  • a general formula for these compounds is: ##STR7##
  • R 2 contains an alkyl, alkenyl, or hydroxy alkyl radical of from about 8 to about 18 carbon atoms, from 0 to about 10 ethylene oxide moieties and from 0 to about 1 glyceryl moiety;
  • Y is selected from the group consisting of nitrogen, phosphorus, and sulfur atoms;
  • R 3 is an alkyl or monohydroxyalkyl group containing about 1 to about 3 carbon atoms;
  • X is 1 when Y is a sulfur atom, and 2 when Y is a nitrogen or phosphorus atom;
  • R 4 is an alkylene or hydroxyalkylene of from about 1 to about 4 carbon atoms and Z is a radical selected from the group consisting of carboxylate, sulfonate, sulfate, phosphonate, and phosphate groups.
  • surfactants examples include:
  • Amphoteric detergents which may be used in this invention include at least one acid group. This may be a carboxylic or a sulphonic acid group. They include quaternary nitrogen and therefore are quaternary amido acids. They should generally include an alkyl or alkenyl group of 7 to 18 carbon atoms. They will usually comply with an overall structural formula: ##STR8##
  • R 1 is alkyl or alkenyl of 7 to 18 carbon atoms
  • R 2 and R 3 are each independently alkyl, hydroxyalkyl or carboxyalkyl of 1 to 3 carbon atoms;
  • n 2 to 4;
  • n 0 to 1;
  • X is alkylene of 1 to 3 carbon atoms optionally substituted with hydroxyl
  • Y is --CO 2 -- or --SO 3 --
  • Suitable amphoteric detergents within the above general formula include simple betaines of formula: ##STR9##
  • R 1 , R 2 and R 3 are as defined previously.
  • R 1 may in particular be a mixture of C 12 and C 14 alkyl groups derived from coconut so that at least half, preferably at least three quarters of the groups R 1 have 10 to 14 carbon atoms.
  • R 2 and R 3 are preferably methyl.
  • amphoteric detergent is a sulphobetaine of formula ##STR11##
  • R 1 , R 2 and R 3 are as discussed previously.
  • amphoteric detergent is a sulphobetaine of formula ##STR13##
  • R 1 , R 2 and R 3 are as discussed previously.
  • Amphoacetates and diamphoacetates are also intended to be covered in possible zwitterionic and/or amphoteric compounds which may be used.
  • the amphoteric/zwitterionic generally comprises 0.1 to 20% by weight, preferably 0.5% to 15%, more preferably 1.0 to 10% by wt. of the composition.
  • the surfactant system may optionally comprise a nonionic surfactant.
  • the nonionic which may be used includes in particular the reaction products of compounds having a hydrophobic group and a reactive hydrogen atom, for example aliphatic alcohols, acids, amides or alkyl phenols with alkylene oxides, especially ethylene oxide either alone or with propylene oxide.
  • Specific nonionic detergent compounds are alkyl (C 6 -C 22 ) phenols-ethylene oxide condensates, the condensation products of aliphatic (C 8 -C 18 ) primary or secondary linear or branched alcohols with ethylene oxide, and products made by condensation of ethylene oxide with the reaction products of propylene oxide and ethylenediamine.
  • Other so-called nonionic detergent compounds include long chain tertiary amine oxides, long chain tertiary phosphine oxides and dialkyl sulphoxides.
  • the nonionic may also be a sugar amide, such as a polysaccharide amide.
  • the surfactant may be one of the lactobionamides described in U.S. Pat. No. 5,389,279 to Au et al. which is hereby incorporated by reference or it may be one of the sugar amides described in U.S. Pat. No. 5,009,814 to Kelkenberg, hereby incorporated into the subject application by reference.
  • alkyl polysaccharides are alkylpolyglycosides of the formula
  • R is selected from the group consisting of alkyl, alkylphenyl, hydroxyalkyl, hydroxyalkylphenyl, and mixtures thereof in which alkyl groups contain from about 10 to about 18, preferably from about 12 to about 14, carbon atoms; n is 0 to 3, preferably 2; t is from 0 to about 10, preferably 0; and x is from 1.3 to about 10, preferably from 1.3 to about 2.7.
  • the glycosyl is preferably derived from glucose. To prepare these compounds, the alcohol or alkylpolyethoxy alcohol is formed first and then reacted with glucose, or a source of glucose, to form the glucoside (attachment at the 1-position). The additional glycosyl units can then be attached between their 1-position and the preceding glycosyl units 2-, 3-, 4- and/or 6-position, preferably predominantly the 2-position.
  • the nonionic surfactant can also be a water soluble polymer chemically modified with hydrophobic moiety or moieties.
  • EO-PO block copolymer, hydrophobically modified PEG such as POE(200)-glyceryl-stearate can be included in the formulations claimed by the subject invention.
  • Nonionic comprises 0 to 10% by wt. of the composition.
  • compositions of the invention may include optional ingredients as follows:
  • Organic solvents such as ethanol; auxiliary thickeners, such as carboxymethylcellulose, magnesium aluminum silicate, hydroxyethylcellulose, methylcellulose, carbopols, glucamides, or Antil® from Rhone Poulenc; perfumes; sequestering agents, such as tetrasodium ethylenediaminetetraacetate (EDTA), EHDP or mixtures in an amount of 0.01 to 1%, preferably 0.01 to 0.05%; and coloring agents, opacifiers and pearlizers such as zinc stearate, magnesium stearate, TiO 2 , EGMS (ethylene glycol monostearate) or Lytron 621 (StyrenelAcrylate copolymer); all of which are useful in enhancing the appearance or cosmetic properties of the product.
  • auxiliary thickeners such as carboxymethylcellulose, magnesium aluminum silicate, hydroxyethylcellulose, methylcellulose, carbopols, glucamides, or Antil® from Rhone Poulenc
  • compositions may further comprise antimicrobials such as 2-hydroxy-4,2'4' trichlorodiphenylether (DP300); preservatives such as dimethyloldimethylhydantoin (Glydant XL1000), parabens, sorbic acid etc.
  • antimicrobials such as 2-hydroxy-4,2'4' trichlorodiphenylether (DP300); preservatives such as dimethyloldimethylhydantoin (Glydant XL1000), parabens, sorbic acid etc.
  • compositions may also comprise coconut acyl mono- or diethanol amides as suds boosters, and strongly ionizing salts such as sodium chloride and sodium sulfate may also be used to advantage.
  • Antioxidants such as, for example, butylated hydroxytoluene (BHT) may be used advantageously in amounts of about 0.01% or higher if appropriate.
  • BHT butylated hydroxytoluene
  • Cationic conditioners which may be used include Quatrisoft LM-200 Polyquaternium-24, Merquat®-polymer; and Jaguar® type conditioners from Rhone-Poulenc; and Salcare®-type conditioners from Allied Colloids.
  • Polyethylene glycols which may be used include:
  • PEG with molecular weight ranging from 300 to 10,000 Dalton such as those marketed under the tradename of CARBOWAX SENTRY® by Union Carbide.
  • exfoliants such as polyoxyethylene beads, walnut shells and apricot seeds
  • the structurant of the invention can be a water soluble or water insoluble structurant.
  • Water soluble structurants include moderately high molecular weight polyalkylene oxides of appropriate melting point (e.g., 40° to 100° C., preferably 50° to 90° C.) and in particular polyethylene glycols or mixtures thereof.
  • Polyethylene glycols which are used may have a molecular weight in the range 2,000 to 25,000, preferably 3,000 to 10,000. However, in some embodiments of this invention it is preferred to include a fairly small quantity of polyethylene glycol with a molecular weight in the range from 50,000 to 500,000, especially molecular weights of around 100,000. Such polyethylene glycols have been found to improve the wear rate of the bars. It is believed that this is because their long polymer chains remain entangled even when the bar composition is wetted during use.
  • the quantity is preferably from 1% to 5%, more preferably from 1% to 1.5% to 4% or 4.5% by weight of the composition.
  • these materials will generally be used jointly with a large quantity of other water soluble structurant such as the above mentioned polyethylene glycol of molecular weight 2,000 to 25,000, preferably 3,000 to 10,000.
  • Water insoluble structurants also have a melting point in the range 40°-100° C., more preferably at least 50° C., notably 50° C. to 90° C.
  • Suitable materials which are particularly envisaged are fatty acids, particularly those having a carbon chain of 12 to 24 carbon atoms. Examples are lauric, myristic, palmitic, stark, arachidic and behenic acids and mixtures thereof. Sources of these fatty acids are coconut, topped coconut, palm, palm kernel, babassu and tallow fatty acids and partially or fully hardened fatty acids or distilled fatty acids.
  • Other suitable water insoluble structurants include alkanols of 8 to 20 carbon atoms, particularly cetyl alcohol. These materials generally have a water solubility of less than 5 g/liter at 20° C.
  • Soaps e.g., sodium stearate
  • Soaps can also be used at levels of about 1% to 15%.
  • the soaps may be added neat or made in situ by adding a base, e.g., NaOH, to convert free fatty acids.
  • the relative proportions of the water soluble structurants and water insoluble structurants govern the rate at which the bar wears during use.
  • the presence of the water-insoluble structurant tends to delay dissolution of the bar when exposed to water during use and hence retard the rate of wear.
  • Another optional ingredient is oil/emollient which may be added as a benefit agent to the bars compositions.
  • Vegetable oils Arachis oil, castor oil, cocoa butter, coconut oil, corn oil, cotton seed oil, olive oil, palm kernel oil, rapeseed oil, safflower seed oil, sesame seed oil and soybean oil.
  • Esters Butyl myristate, cetyl palmitate, decyloleate, glyceryl laurate, glyceryl ricinoleate, glyceryl stearate, glyceryl isostearate, hexyl laurate, isobutyl palmitate, isocetyl stearate, isopropyl isostearate, isopropyl laurate, isopropyl linoleate, isopropyl, myristate, isopropyl palmitate, isopropyl stearate, propylene glycol monolaurate, propylene glycol ricinoleate, propylene glycol stearate, and propylene glycol isostearate.
  • Animal Fats Acytylated lanolin alcohols, lanolin, lard, mink oil and tallow.
  • Fatty acids and alcohols Behenic acid, palmitic acid, stearic acid, behenyl alcohol, cetyl alcohol, eicosanyl alcohol and isocetyl alcohol.
  • oil/emollients include mineral oil, petrolatum, silicone oil such as dimethyl polysiloxane, lauryl and myristyl lactate.
  • the emollient/oil is generally used in an amount from about 1 to 20%, preferably 1 to 15% by wt. of the composition. Generally, it should comprise no more than 20% of the composition.
  • compositions of the invention should comprise no more than 1%, and should more preferably be free of inorganic or organic salts of multivalent metal counterions.
  • metal counterions are defined as having valence of +2 or higher and include counterions such as calcium, magnesium and aluminum.
  • salts include, for example, aluminum chloride, magnesium chloride, calcium chloride and magnesium laurels. While not wishing to be bound by theory, it is believed essential to keep the amount of such counterions low or absent so that they don't interfere with lather performance of EDTA-derived anionic surfactant.
  • the invention relates to a process of making the composition of the invention to ensure that EDTA-derived surfactant is incorporated, provides desired mildness characteristics and that latherability is not at the same time compromised.
  • process comprises:
  • This in situ neutralization process is necessary to avoid gelling of the EDTA derived surfactant.
  • the gelling which occurs in an aqueous solution, prevents a homogeneous mixing of the ingredients.
  • Zein dissolution test was used to preliminary screen the irritation potention of the formulations studied.
  • 30 mLs of an aqueous dispersion of a formulation were prepared.
  • the dispersions sat in a 45° C. bath until fully dissolved.
  • 1.5 gms of zein powder were added to each solution with rapid stirring for one hour.
  • the solutions were then transferred to centrifuge tubes and centrifuged for 30 minutes at approximately 3,000 rpms.
  • the undissolved zein was isolated, rinsed and allowed to dry in 60° C. vacuum oven to a constant weight.
  • the percent zein solubilized which is proportional to irritation potential, was determined gravimetrically.
  • the Lather Volume Measurement The lather performance was studied by a cylinder shaking test. Forty grams of a test solution was put in a 250 ml PYREX cylinder with cap. Foam was generated by shaking the cylinder for 0.5 minute. After the foam settled for 2.5 minutes, the foam height was measured.
  • Na-LED3A The skin irritation potential of Na-LED3A was investigated by the zein dissolution test. As shown in Table 1, Na-LED3A dissolved significantly less amount of zein than commonly used anionic surfactants, such as sodium cocoyl isethionate and sodium lauryl ether (3EO) sulfate. The result indicates that the sodium lauroyl EDTA is an ultra-mild anionic surfactant to skin.
  • anionic surfactants such as sodium cocoyl isethionate and sodium lauryl ether (3EO) sulfate.
  • EDTA Derived Surfactants Sodium lauroyl EDTA (named as Na-LED3A) was obtained through neutralizing N-lauroyl-N, N'N'-ethylenediaminetriacetic (Hampshire, under the trade name of LED3A) using 50% sodium hydroxide (NaOH) solution.
  • LED3A was first dispersed and mixed in molten polyethylene glycol 8000 at a temperature between 80° C. and 120° C. A precalculated amount of sodium hydroxide solution (50%) was slowly added to neutralize the LED3A. After adequate mixing, the remaining ingredients were added. This in-situ process was used to avoid the gelling of EDTA-derived surfactants in an aqueous solution (gelling occurs at concentrations between 40% and 79% by weight in water) which prevents a homogeneous mixing of the bar material.
  • Formulation Processing Formulations shown in the examples of this invention were prepared in 400 mL beakers in a 100° C. oil bath. Mixing was accomplished with a variable speed overhead motor. Batch size was varied from 100-250 gms. All chemicals used except the EDTA derived surfactants were commercial materials and used as supplied.
  • the lather performance of the Na-LED3A aqueous solution is not as satisfactory as those commonly used anionic surfactants, such as sodium lauryl ether (3EO) sulfate. As shown in Table 3, the lather volume of the 2.5% Na-LED3A is significantly less than that of SLES. However, by adding relatively low levels of SLES and Cocoamidopropyl betaine as coactives to the Na-LED3A solution, the lather performance was greatly improved. This example demonstrates the necessity of inclusion of anionic and amphoteric surfactants into an EDTA-derived surfactant based skin cleanser.
  • Table 4 shows the lather volumes of bar formulations which are composed of Na-LED3A. This example demonstrates that acceptable lather performance is achieved when the chelating surfactant is incorporated in bar formulations.
  • Organic and inorganic salts containing multi-valence salts such as Aluminum Chloride, Magnesium Chloride, Calcium Chloride, Calcium stearate, Magnesium laurate, etc. are often used in personal washing products.
  • these multi-valence salts can interact with the EDTA-derived surfactants and cause defoaming if the salt concentration is above 1% wt. total composition. As shown in Table 2, 2.5% salts significantly defoamed the EDTA-derived surfactant. Therefore, preferably, these multi-valence salts are excluded from the skin cleansing compositions claimed by this invention.
  • Formulations (A), (B) and (C) used sodium cocoyl isethionate and Na-LED3A as the major anionic detergent with amphoteric cocoamidopropyl betaine as a coactive.
  • the formulations provide rich, creamy, and slippery lather that was rinsed off easily.

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US08/869,397 1997-06-05 1997-06-05 Bar compositions comprising novel chelating surfactants Expired - Fee Related US5869441A (en)

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US08/869,397 US5869441A (en) 1997-06-05 1997-06-05 Bar compositions comprising novel chelating surfactants
EP98932097A EP0986628B1 (en) 1997-06-05 1998-05-22 Bar compositions comprising novel chelating surfactants and related process for manufacture of such bars
CA002291029A CA2291029A1 (en) 1997-06-05 1998-05-22 Bar compositions comprising novel chelating surfactants and related process for manufacture of such bars
AU82114/98A AU8211498A (en) 1997-06-05 1998-05-22 Bar compositions comprising novel chelating surfactants and related process for manufacture of such bars
ES98932097T ES2183388T3 (es) 1997-06-05 1998-05-22 Composiciones de pastillas de jabon que contienen nuevos tensioactivos quelantes y procedimientos relacionados para fabricar tales pastillasde jabon.
PCT/EP1998/003184 WO1998055571A1 (en) 1997-06-05 1998-05-22 Bar compositions comprising novel chelating surfactants and related process for manufacture of such bars
DE69807686T DE69807686T2 (de) 1997-06-05 1998-05-22 Neue chelatierende tenside enthaltende stückzusammensetzungen und verfahren zu deren erzeugung
IN345BO1998 IN189873B (enrdf_load_stackoverflow) 1997-06-05 1998-06-03
ZA9804898A ZA984898B (en) 1997-06-05 1998-06-05 Bar compositions comprising chelating surfactants and related process for manufacture of such bars.
ARP980102668A AR015386A1 (es) 1997-06-05 1998-06-05 Composiciones en barra que comprenden nuevos tensioactivos quelantes y un procedimiento para la fabricacion de tales barras.

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US08/869,397 US5869441A (en) 1997-06-05 1997-06-05 Bar compositions comprising novel chelating surfactants

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US5869441A true US5869441A (en) 1999-02-09

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US (1) US5869441A (enrdf_load_stackoverflow)
EP (1) EP0986628B1 (enrdf_load_stackoverflow)
AR (1) AR015386A1 (enrdf_load_stackoverflow)
AU (1) AU8211498A (enrdf_load_stackoverflow)
CA (1) CA2291029A1 (enrdf_load_stackoverflow)
DE (1) DE69807686T2 (enrdf_load_stackoverflow)
ES (1) ES2183388T3 (enrdf_load_stackoverflow)
IN (1) IN189873B (enrdf_load_stackoverflow)
WO (1) WO1998055571A1 (enrdf_load_stackoverflow)
ZA (1) ZA984898B (enrdf_load_stackoverflow)

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US6462004B2 (en) 2000-08-03 2002-10-08 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Synthetic bar compositions providing source of divalent cations available at critical point to enhance bar processing
US20030113364A1 (en) * 1997-05-22 2003-06-19 The Procter & Gamble Company Cleansing articles for skin or hair
US20030228351A1 (en) * 2002-06-07 2003-12-11 The Procter & Gamble Company Cleansing articles for skin or hair
US20030228352A1 (en) * 2002-06-07 2003-12-11 The Procter & Gamble Company Cleansing articles for skin or hair
US20040127372A1 (en) * 2002-12-23 2004-07-01 Ketelson Howard Allen Use of multifunctional surface active agents to clean contact lenses
US20050014654A1 (en) * 2003-07-18 2005-01-20 Qi Qu Method of reclaiming brine solutions using an organic chelant
US20050201965A1 (en) * 2004-03-11 2005-09-15 The Procter & Gamble Company Personal cleansing compositions
US20050227875A1 (en) * 2003-07-18 2005-10-13 Bj Services Company Method of reclaiming brine solutions using an organic chelant
US20070131623A1 (en) * 2003-07-18 2007-06-14 Bj Services Company Method of reclaiming brine solutions using an organic chelant
US20070138101A1 (en) * 2003-07-18 2007-06-21 Bj Services Company Method of reclaiming brine solutions using an organic chelant
US20100130770A1 (en) * 2008-11-12 2010-05-27 Irix Pharmaceuticals N-alkanoyl-n,n',n'-alkylenediamine trialkanoic acid esters

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US20050075255A1 (en) * 1997-05-22 2005-04-07 The Procter & Gamble Company Methods of cleansing skin or hair with cleansing articles
US20030113364A1 (en) * 1997-05-22 2003-06-19 The Procter & Gamble Company Cleansing articles for skin or hair
US7348018B2 (en) 1997-05-22 2008-03-25 The Procter & Gamble Company Methods of cleansing skin or hair with cleansing articles
US6955817B2 (en) 1997-05-22 2005-10-18 The Procter & Gamble Company Cleansing articles for skin or hair
US6462004B2 (en) 2000-08-03 2002-10-08 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Synthetic bar compositions providing source of divalent cations available at critical point to enhance bar processing
US7115551B2 (en) 2002-06-07 2006-10-03 The Procter & Gamble Company Cleansing articles for skin or hair
US20030228351A1 (en) * 2002-06-07 2003-12-11 The Procter & Gamble Company Cleansing articles for skin or hair
US20030228352A1 (en) * 2002-06-07 2003-12-11 The Procter & Gamble Company Cleansing articles for skin or hair
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US20040127372A1 (en) * 2002-12-23 2004-07-01 Ketelson Howard Allen Use of multifunctional surface active agents to clean contact lenses
US20050282715A1 (en) * 2002-12-23 2005-12-22 Ketelson Howard A Use of multifunctional surface active agents to clean contact lenses
US7172703B2 (en) 2003-07-18 2007-02-06 Bj Services Co Method of reclaiming a well completion brine solutions using an organic chelant
US20050227875A1 (en) * 2003-07-18 2005-10-13 Bj Services Company Method of reclaiming brine solutions using an organic chelant
US7144512B2 (en) 2003-07-18 2006-12-05 Bj Services Company Method of reclaiming brine solutions using an organic chelant
US20050014654A1 (en) * 2003-07-18 2005-01-20 Qi Qu Method of reclaiming brine solutions using an organic chelant
US20070095762A1 (en) * 2003-07-18 2007-05-03 Qi Qu Method of reclaiming brine solutions using an organic chelant
US20070131623A1 (en) * 2003-07-18 2007-06-14 Bj Services Company Method of reclaiming brine solutions using an organic chelant
US20070138101A1 (en) * 2003-07-18 2007-06-21 Bj Services Company Method of reclaiming brine solutions using an organic chelant
US7674384B2 (en) 2003-07-18 2010-03-09 Bj Services Company Method of reclaiming brine solutions using an organic chelant
US7678281B2 (en) 2003-07-18 2010-03-16 Bj Services Company Method of reclaiming brine solutions using an organic chelant
US20080031842A1 (en) * 2004-03-11 2008-02-07 Kuhlman Dennis E Personal cleansing compositions
US20050201965A1 (en) * 2004-03-11 2005-09-15 The Procter & Gamble Company Personal cleansing compositions
US20100130770A1 (en) * 2008-11-12 2010-05-27 Irix Pharmaceuticals N-alkanoyl-n,n',n'-alkylenediamine trialkanoic acid esters
US8258334B2 (en) 2008-11-12 2012-09-04 Irix Pharmaceuticals, Inc. N-alkanoyl-N,N′,N′-alkylenediamine trialkanoic acid esters

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AR015386A1 (es) 2001-05-02
DE69807686T2 (de) 2003-06-05
IN189873B (enrdf_load_stackoverflow) 2003-05-03
WO1998055571A1 (en) 1998-12-10
EP0986628B1 (en) 2002-09-04
AU8211498A (en) 1998-12-21
DE69807686D1 (de) 2002-10-10
CA2291029A1 (en) 1998-12-10
EP0986628A1 (en) 2000-03-22
ES2183388T3 (es) 2003-03-16
ZA984898B (en) 1999-12-06

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